The Uchiha Dilemma
by HiddenBehindCrimsonEyes
Summary: Sakura is Sasuke's bestfriend. What happens when Itachi suddenly takes an interest in her? How would Sasuke react? AU. ItaSaku.
1. Prologue

**The Uchiha Dilemma**

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**Disclaimer: _I do not own Naruto. _**

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**Prologue **

The Uchiha Corporation is one of the worlds largest companies. They have a hand in almost every industry, from car companies to make-up industries, from shipping to publishing, and just about everything else there is. And this company's owner is none other than Uchiha Fugaku, along with his beautiful bride, Uchiha Mikoto.

Fugaku and Mikoto reared two children: Uchiha Sasuke and their eldest Uchiha Itachi.

Uchiha Itachi is the epitome of the 'prince' that women dream of. He is devastatingly handsome, has a physique that could make a Greek god weep with envy, and long black locks and beautiful skin that women would spend thousands to have. He is lauded for his prodigious intelligence and photographic memory. His skills in martial arts are unparalleled; surpassing his masters by the age of 12. His voice has an almost hypnotic timbre to it that could make anyone do almost anything he asks. He has the demeanor of a prince, the perfect gentleman. And to top it all off he can cook mouthwatering morsels. It seems that Uchiha Itachi can do everything. Because of this, women are drawn to Itachi like moths to a flame. And Itachi, the playboy he is, is more than happy to entertain them.

His younger brother Uchiha Sasuke, is 6 years younger than he and is bestowed just about everything he has_** (A/N: well... except for the long black hair but you knew that already, didn't you?).**_ But unlike him, his bother is a bit on the emo-side, and exudes the bad boy aura like a factory spouts fumes. Though fame follows him like a puppy, he is a bit anti-social and avoids the members of the opposite sex like the plague. In his school, Hoshi Gakuen, he is deemed the most popular guy in the campus, as he is the Student Council's Vice Chairman and the basketball team's ace player. Though seemingly _**gynophobic, **_Sasuke's best friend is a female, and her name is Haruno Sakura.

To Haruno Sakura fell the position and the responsibilities of the Student Council Chairman. And though she is by far as popular as Sasuke is, she had never had a boyfriend or, for that matter, another male friend other than her overprotective best friends, Uchiha Sasuke and Namikaze Naruto.

No man was stupid enough to risk the wrath of Naruto and Sasuke by asking her out. That is until Itachi Uchiha noticed the his little brother's best friend.

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**A/N: R****eviews are appreciated**

**By the way **_**Gynophobia ****means**__**Fear of or contempt for women.**_


	2. Chapter 1: Advent of Interest

**The Uchiha Dilemma**

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Disclaimer: _I do not own Naruto…_

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_**Chapter 1: Advent of Interest**_

Sakura stood between her two best friends, her long pink hair flowing in the wind as they watch the sun set beneath the horizon from the rooftop of Hoshi Gakuen's enormous five-story library, as they have done for the past five years.

'But today somehow, something feels different…' Sakura thought as she smiled at her dark haired best friend.

"Sasuke" she called, "What's got you in such a great mood?"

"Yeah, Sasuke-teme!" the exuberant blond added. "Usually, you're already in a pissy mood by noon, but now you're still smiling and it's already six in the afternoon."

He then continued with an overdramatic shiver. "Frankly, it's creepy, seeing you smile so much."

Sasuke sighed deeply, but choose to ignore the blue-eyed idiot's comment and replied in his dull monotone, "Aniki's returning tomorrow."

Sakura smiled softly, shaking her head slightly.

Sasuke had always looked up to his genius older brother. Heck, he practically worshipped the ground Itachi walked on. He did almost everything Itachi did. But when his older brother left for Yale University four years ago, the hero-worship disappeared. But now it seems that sooner or later it will come back in full force.

"Anou… okaa-san's inviting the two of you to aniki's welcome party tomorrow evening." Sasuke said. "I'll pick-up both of you at Sakura's by seven. Don't be late, dobe."

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The next evening Sasuke was pacing about sakura's living room, his annoyance evident from the more-prominent-than-normal scowl marring his handsome features because they are already 45 minutes late. And Sakura still hadn't emerged from the confines of her bedroom.

"Neh, Sakura-chan~~" Naruto whined loudly, a childish pout on his lips. "Hurry up already. We're late! Mikoto-baa-chan's going to have my hide."

"Hai, hai." Sakura called. "I'm almost done."

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Itachi stood amongst the myriad of guests that had arrived for his welcome party, genially greeting and conversing with them, a breathtaking smile across his features. But inwardly, he was scowling, annoyed that he has to play the genial, gentlemanly host in a party he didn't even want. He was sorely against this party, but his mother insisted. And when Mikoto Uchiha wanted something, not even her stoic husband can keep her from it.

But what annoyed him most was that it was almost two hours into the party and his little brother was nowhere in sight.

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When the blue Mercedes arrived, Itachi fought a sigh of relief, excused himself from the female currently accosting him, and walked towards the entrance.

As soon as Sasuke stepped out of the car, he called out, "Sasuke, you're extremely late. I almost thought you didn't want to see me."

Sasuke stared at his brother for a moment and then, in a rare display of childish behavior, stuck his tongue out.

Then Naruto said, "Neh, neh, Sakura-chan! Did you see that? Did teme just stick his tongue out?"

Itachi turned to look at them just in time to see Sakura roll her eyes at her blond friend's behavior.

"Itachi-san." Sakura said. "Please excuse Naruto's behavior. I'm afraid he has the maturity of an eight year old."

Sakura's comment was followed by an indignant "Hey! I do not have the maturity of an eight year old." By Naruto.

"Yeah." Sasuke said. "Dobe's more like a five year old."

"Yeah!" Naruto agreed, then looked confused for a moment, then yelled. "HEY!"

Sasuke just smirked and Sakura muttered, "It seems Sasuke's maturity is just about the same." Then she turned to Itachi and said, "Please excuse their pre-adolescent behavior."

Itachi then chuckled softly then said, "I'm Sasuke's aniki, you know? You don't have to apologize for their… antics."

Sakura then smiled and said, "Sorry… knee-jerk reaction."

"Knee-jerk reaction?" Itachi repeated, amused.

"Yeah." Sakura replied, then added, "If you'll excuse me, I have to go great Mikoto baa-chan."

Sakura started to walk towards his mother, but then she stopped, turned to face him and said, "And… Itachi-san welcome back." With a warm smile on her face before she continued on to greet his mother.

What Sakura did caught him off guard, Itachi was startled by the beauty of her smile and the warmth of her greeting. Even though he had repeatedly heard those words throughout the night, it seems as though only Sakura's greeting reached him. And that night he repeatedly caught himself watching her.

Before long he had noticed the changes in her that happened in her during the years that he was gone. No longer was she the self-conscious 15 year old he used to know, now she had bloomed into a confident and beautiful young woman. She had the demeanor of a princess, and it was funny to watch her keep her two best friends in line with nothing but a stern look or a concealed warning. When four years ago she would immediately resort to brute force, now one would see her watching them fight with amusement dancing in her eyes before she would sigh and pull them apart.

It was also amazing how beautiful she had become within the short years that he was away. Her vibrant pink hair now reaching past her waist, her green eyes had never failed to light up with her every emotion, her expressive and beautifully angelic features.

'Her body had grown, too.' He thought appreciatively, as he gave her body a discrete visual inspection.

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Sasuke noticed that Itachi's attention was focused elsewhere. Curious as to what could so completely capture his aniki's attention, he followed Itachi's line of sight. And when he realized the answer to his query, a frown soon crept upon his features.

He then stood beside his aniki and said, "Aniki, I know that look."

"Hmm??" was his older brother's amused reply.

"If you're just planning on adding Sakura to your ever-expanding list of conquests, I suggest you rethink that course of action."

"Protective, aren't we Sasuke-chan?" Itachi replied, amusement dancing clearly in his eyes.

"Aniki… I'm not joking. If you hurt Sakura, I will turn your worst nightmare into reality… and I'm sure Shisui-niisan won't mind helping me."

_**To be continued…**_

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**Author's Note: Reviews are appreciated…**


	3. Chapter 2: Admitting Adoration

**Chapter 2: Admitting Adoration**

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It was already well past three in the morning by the time Itachi's welcome party concluded, and the first rays of sunlight were already shining past the horizon by the time Sakura, Naruto, and Sasuke escaped the overenthusiastic hostess that was the Uchiha matriarch. That was why it was already half-past five when Naruto and Sakura boarded the midnight blue Mercedes to be driven home by its grumpier-than-usual owner, Sasuke.

Sakura found it very odd that Sasuke, after meeting his older brother that he practically worshipped, was in a bad mood, but, in her exhaustion-dimmed thoughts, chalked it up to that during the entire night Sasuke got to spend all of five minutes with his beloved aniki. But in her preoccupation with Sasuke's weird behavior, she missed the wonder that is Naruto's complete silence.

They dropped Sakura off first, and as soon as the car pulled away from the Haruno house's driveway, Naruto, who was previously unnervingly quiet during the trip, asked, "Neh, Sasuke-teme, what's got you so grumpy? You're even grumpier than the Grinch on Christmas."

To which Sasuke's only reply was, predictably, an annoyed grunt.

"Ahh… I know! I know!" Naruto exclaimed, "You're jealous because Sakura-chan got to spend more time with Itachi than you did!"

Sasuke merely rolled his eyes, too tired to participate in whatever game the blond idiot's trying to goad him into playing.

Seeing Sasuke's reaction the hyperactive blond muttered, "So that's not it, eh?". Then he promptly became completely silent, to which Sasuke was thankful for.

Then a few minutes later, Naruto yelled, in a volume that only he is capable of, "Oh~~ I got it, teme! I got it! I got it! I—"

"Fine, fine", Sasuke sighed in annoyance and said, "What now?"

"You're jealous cuz" Naruto said, "Itachi got to spend the whole night dancing…"

…Sasuke remembered how Itachi held Sakura while they danced…

"…and chatting…"

…the way she smiled at his aniki while they talked…

"…and flirting with Sakura-chan."

…the way she flushed a pretty pink when he complimented her.

Sasuke kept his stoic façade but Naruto noticed him stiffen ever so slightly and his grip on the steering wheel tighten almost imperceptively.

"So that's it?" Naruto laughed loudly, very loudly, "I got it right!" he teased. "I always knew you had the hots for Sakura-chan!"

"Shut up, dobe." Sasuke muttered, his voice calm and quiet, but the mere fact that he bothered to speak up and answer was confirmation enough for his best friend.

Naruto ignored Sasuke's request or – to put it more accurately – took it as an encouragement and continued to speak his mind, "You know, teme, you were never very good at hiding it anyway."

Sasuke's posture stiffened further at that remark.

"You always stare at her when you think no one's looking.  
You've always enjoyed scaring off her suitors way too much, frankly it's really creepy.  
You worry way too much when she's sick. So much that you even managed to fail a math exam. I mean math, teme! Your favorite subject!  
You always blush when she kisses your cheek. But I've seen you ignore a girl who stripped to her birthday suit just to get your attention.  
And I've—"

"Alright! I get it already! Okay!" Sasuke yelled in an uncharacteristic display of anger and frustration. "I wasn't good at hiding it!"

Naruto kept silent for a moment or two obviously not expecting Sasuke's outburst.

"So teme… what are you gonna do then?" Naruto said. "It seems that Itachi has his sights set on Sakura, and you and I both know that no one's ever turned down Itachi."

"I don't know… I honestly don't know." He replied resigned. "I guess we'll just have to hope that she'll be the first."

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A/N: Sorry for the short chapter. I am suffering from writer's block, because of the rapid succession of examinations and my extracurricular responsibilities. But all those are just excuses. I just really have writers block. Be thankful to my friend who nagged me endlessly to post this. Or the next time I would have posted a chapter might have been somewhere in July…


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